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The title compound, C15H25Cl, was semi-synthesized from natural essential oils of Cedrus atlantica. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The asymmetric unit contains two chemically identical mol­ecules. Each is built up from two fused six- and seven-membered rings. In both mol­ecules, the six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a twist-chair conformation. In one mol­ecule, the seven-membered ring is partially disordered with a site-occupancy ratio of 0.52:0.48.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037403/cs2043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037403/cs2043Isup2.hkl
Contains datablock I

CCDC reference: 660192

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.132
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.756 1.000 Tmin(prime) and Tmax expected: 0.851 0.950 RR(prime) = 0.844 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 14 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 14.90 Deg. C8A -C7A -C8B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.20 Deg. C15B -C11A -C15A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.10 Deg. C10B -C11A -C10A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.00 Deg. C14A -C11A -C14B 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.950 Tmax scaled 0.950 Tmin scaled 0.718 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.10 From the CIF: _reflns_number_total 6222 Count of symmetry unique reflns 3574 Completeness (_total/calc) 174.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2648 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6A = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The isolated sesquiterpenes of Cedrus atlantica essential oils were the subject of hemisynthesis in order to prepare chlorinated sesquiterpenoid compounds (El Jamili et al., 2002; Dakir et al., 2004) in good yield. Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al., 2005). Other molecules containing chlorine atom induces stalk-cell differentiation during development of Dictystelium discoideum (Kav et al., 1992).

We were interested in the study on the reactivity of compound (A) (Ourhriss et al., 2007) which has two chlorine atoms at different positions, 3 and 7 (Fig. 1). The dehydrohalogenation of (A) gave, after heating at reflux in methanol, the title compound (I) with high chemoselectivity. 1H and 13C NMR spectroscopy did not make it possible to identify the exact structure of this product. Single-crystal X-ray diffraction analysis allowed us to elucidate its configuration and to identify (I) as (1S,3R,6S)-3-chloro-trans-himachalene.

The molecule is built up from two fused six-membered and seven-membered rings (Fig. 2). The six membered ring has a perfect chair conformation as indicated by the total puckering amplitude QT= 0.560 (3) Å[0.546 (3) Å] and spherical polar angle θ=168.4 (3)° [174.1 (3)°] with φ= 117 (2)°[121 (3)°] whereas the seven-membered ring in the non disordered molecule displays a twist-chair conformation with QT= 0.807 (7) Å, θ= 36.7 (7)°, φ2= -179.8 (5)° and φ3= 120.8 (3)° (Cremer & Pople, 1975).

Owing to the presence of the Cl atom, the absolute configuration could be fully confirmed to be C1(S), C3(R) and C6(S) (Flack, 1983).

Related literature top

For general background see: El Jamili et al. (2002); Dakir et al. (2004); Daoubi et al. (2005); Kav et al. (1992). For a related structure see: Ourhriss et al. (2007). For related literature, see: Cremer & Pople (1975).

Experimental top

1 g (4.16 mmol) of compound (A) was dissolved in 15 ml of methanol. The mixture was heated until total dissolution, and then left resting at 0°C for 1 h. All this allowed us, after filtering under reduced pressure, to prepare (1S,3R,6S)-3-chloro-trans-himachalene, (I) in 84% yield. Suitable crystals were obtained by evaporation of a hexane solution at 277 K. m.p. = 325–326 K (hexane); Spectroscopic analysis: 1H NMR (300 MHz, CDCl3) δ (p.p.m.):1.63 (3H12, s), 4.65, 4.67 (Ha-13, Hb-13, 2 s), 0.80, 0.90 (3H14, 3H15, 2 s); 13C NMR (75 MHz, CDCl3) δ (p.p.m.): 47.9 (C-1), 43.0 (C-2), 72.0 (C-3), 42.9 (C-4), 24.4 (C-5), 43.3 (C-6), 155.9 (C-7), 41.5 (C-8), 32.9 (C-9), 31.7 (C-10) 43.4 (C-11), 34.7 (C-12), 110.5 (C-13), 30.2 (C-14), 22.3 (C-15).

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (CH2), 1.0 Å(CH) or 0.98 Å (CH3) with Uiso(H) = 1.2Ueq(CH, CH2) or Uiso(H) = 1.5Ueq(CH3).

Structure description top

The isolated sesquiterpenes of Cedrus atlantica essential oils were the subject of hemisynthesis in order to prepare chlorinated sesquiterpenoid compounds (El Jamili et al., 2002; Dakir et al., 2004) in good yield. Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al., 2005). Other molecules containing chlorine atom induces stalk-cell differentiation during development of Dictystelium discoideum (Kav et al., 1992).

We were interested in the study on the reactivity of compound (A) (Ourhriss et al., 2007) which has two chlorine atoms at different positions, 3 and 7 (Fig. 1). The dehydrohalogenation of (A) gave, after heating at reflux in methanol, the title compound (I) with high chemoselectivity. 1H and 13C NMR spectroscopy did not make it possible to identify the exact structure of this product. Single-crystal X-ray diffraction analysis allowed us to elucidate its configuration and to identify (I) as (1S,3R,6S)-3-chloro-trans-himachalene.

The molecule is built up from two fused six-membered and seven-membered rings (Fig. 2). The six membered ring has a perfect chair conformation as indicated by the total puckering amplitude QT= 0.560 (3) Å[0.546 (3) Å] and spherical polar angle θ=168.4 (3)° [174.1 (3)°] with φ= 117 (2)°[121 (3)°] whereas the seven-membered ring in the non disordered molecule displays a twist-chair conformation with QT= 0.807 (7) Å, θ= 36.7 (7)°, φ2= -179.8 (5)° and φ3= 120.8 (3)° (Cremer & Pople, 1975).

Owing to the presence of the Cl atom, the absolute configuration could be fully confirmed to be C1(S), C3(R) and C6(S) (Flack, 1983).

For general background see: El Jamili et al. (2002); Dakir et al. (2004); Daoubi et al. (2005); Kav et al. (1992). For a related structure see: Ourhriss et al. (2007). For related literature, see: Cremer & Pople (1975).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Scheme showing the transformation of compound (A) to the title compound (I)
[Figure 2] Fig. 2. View of compound I with the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level, H atoms are represented as small spheres of arbitrary radii.
(1S,3R,6S)-3-Chloro-trans-himachalene top
Crystal data top
C15H25ClF(000) = 1056
Mr = 240.80Dx = 1.134 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3489 reflections
a = 6.0470 (2) Åθ = 2.7–32.1°
b = 15.7158 (7) ŵ = 0.25 mm1
c = 29.6845 (12) ÅT = 180 K
V = 2821.02 (19) Å3Prism, colourless
Z = 80.65 × 0.24 × 0.21 mm
Data collection top
Oxford Diffraction CCD Xcalibur
diffractometer
6222 independent reflections
Radiation source: fine-focus sealed tube3666 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 8.2632 pixels mm-1θmax = 27.1°, θmin = 2.7°
ω and φ scansh = 75
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
k = 2020
Tmin = 0.756, Tmax = 1.000l = 3838
23369 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6222 reflectionsΔρmax = 0.41 e Å3
294 parametersΔρmin = 0.39 e Å3
15 restraintsAbsolute structure: Flack (1983), based on 2652 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.11 (7)
Crystal data top
C15H25ClV = 2821.02 (19) Å3
Mr = 240.80Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 6.0470 (2) ŵ = 0.25 mm1
b = 15.7158 (7) ÅT = 180 K
c = 29.6845 (12) Å0.65 × 0.24 × 0.21 mm
Data collection top
Oxford Diffraction CCD Xcalibur
diffractometer
6222 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
3666 reflections with I > 2σ(I)
Tmin = 0.756, Tmax = 1.000Rint = 0.047
23369 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.132Δρmax = 0.41 e Å3
S = 1.01Δρmin = 0.39 e Å3
6222 reflectionsAbsolute structure: Flack (1983), based on 2652 Friedel pairs
294 parametersAbsolute structure parameter: 0.11 (7)
15 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl20.17012 (12)0.00184 (5)0.82920 (3)0.0474 (2)
C10.5574 (5)0.12081 (18)0.87157 (9)0.0324 (7)
H10.40030.12200.88200.039*
C20.5564 (5)0.08395 (17)0.82356 (9)0.0340 (7)
H210.46690.12200.80420.041*
H220.70980.08520.81190.041*
C30.4693 (4)0.00486 (19)0.81847 (10)0.0341 (7)
C40.5669 (5)0.06490 (19)0.85311 (10)0.0394 (8)
H410.72140.07820.84460.047*
H420.48220.11880.85280.047*
C50.5647 (5)0.02863 (17)0.90055 (10)0.0383 (8)
H510.63990.06860.92130.046*
H520.40990.02200.91080.046*
C60.6811 (5)0.05764 (18)0.90211 (9)0.0335 (7)
H60.83010.04900.88820.040*
C70.7212 (6)0.0838 (2)0.95016 (11)0.0456 (9)
C80.5674 (8)0.1440 (2)0.97280 (11)0.0621 (11)
H810.57930.13701.00590.075*
H820.41350.13060.96390.075*
C90.6195 (10)0.2348 (2)0.96037 (12)0.0794 (14)
H910.54660.27270.98250.095*
H920.78100.24340.96330.095*
C100.5521 (7)0.2611 (2)0.91505 (12)0.0606 (11)
H10A0.59040.32210.91190.073*
H10B0.38890.25710.91370.073*
C110.6439 (5)0.21461 (19)0.87306 (10)0.0369 (7)
C120.4969 (6)0.0370 (2)0.77094 (10)0.0480 (9)
H12A0.41880.00100.75010.072*
H12B0.43530.09450.76860.072*
H12C0.65440.03830.76320.072*
C130.8968 (8)0.0533 (2)0.97185 (13)0.0701 (12)
H13A0.92480.07001.00210.084*
H13B0.99410.01480.95710.084*
C140.5492 (6)0.2663 (2)0.83362 (12)0.0525 (9)
H14A0.58890.32640.83730.079*
H14B0.38780.26070.83320.079*
H14C0.61040.24500.80520.079*
C150.8931 (5)0.2188 (2)0.87064 (13)0.0588 (10)
H15A0.94450.18780.84400.088*
H15B0.95650.19280.89770.088*
H15C0.94000.27830.86860.088*
Cl1A0.61711 (12)0.71053 (6)0.79807 (3)0.0478 (2)
C2A1.0131 (5)0.73751 (18)0.83943 (9)0.0317 (7)
H2A10.94270.79100.84960.038*
H2A21.17340.74870.83610.038*
C3A0.9197 (4)0.7146 (2)0.79321 (9)0.0367 (7)
C4A0.9978 (5)0.6273 (2)0.77819 (10)0.0448 (9)
H4A10.91570.61060.75070.054*
H4A21.15670.63050.77030.054*
C5A0.9659 (6)0.5603 (2)0.81364 (10)0.0464 (9)
H5A11.03020.50610.80290.056*
H5A20.80560.55130.81850.056*
C6A1.0739 (5)0.58486 (18)0.85846 (10)0.0371 (8)
H6A1.23560.59270.85280.044*
C7A1.0477 (6)0.5107 (2)0.89092 (12)0.0518 (9)
C8A0.8830 (13)0.5086 (7)0.9265 (2)0.0495 (10)0.52
H8A10.86510.44900.93670.059*0.52
H8A20.73960.52740.91380.059*0.52
C9A0.9364 (13)0.5634 (4)0.9670 (2)0.0495 (10)0.52
H9A10.83070.54910.99130.059*0.52
H9A21.08610.54810.97780.059*0.52
C10A0.9295 (12)0.6582 (4)0.9596 (2)0.0495 (10)0.52
H10C0.96980.68560.98850.059*0.52
H10D0.77370.67360.95340.059*0.52
C11A1.0726 (5)0.70010 (18)0.92240 (9)0.0325 (7)
C14A1.3124 (11)0.6824 (4)0.9264 (3)0.0462 (13)0.52
H14D1.39240.71340.90280.069*0.52
H14E1.33850.62120.92290.069*0.52
H14F1.36490.70100.95600.069*0.52
C15A1.0291 (11)0.7947 (5)0.9304 (3)0.0462 (13)0.52
H15D1.06880.80940.96140.069*0.52
H15E0.87200.80690.92540.069*0.52
H15F1.11850.82850.90950.069*0.52
C1A0.9818 (5)0.67051 (17)0.87616 (9)0.0287 (7)
H1A0.81870.66270.87990.034*
C8B0.8358 (14)0.5152 (7)0.9182 (3)0.0495 (10)0.48
H8B10.79780.45780.92960.059*0.48
H8B20.71320.53490.89870.059*0.48
C9B0.8644 (13)0.5785 (5)0.9593 (3)0.0495 (10)0.48
H9B10.73450.61680.95980.059*0.48
H9B20.86060.54450.98740.059*0.48
C10B1.0686 (13)0.6326 (4)0.9603 (2)0.0495 (10)0.48
H10E1.20020.59560.95740.059*0.48
H10F1.07760.66180.98980.059*0.48
C14B1.3206 (12)0.7264 (5)0.9206 (3)0.0462 (13)0.48
H14G1.37600.73490.95130.069*0.48
H14H1.33560.77950.90350.069*0.48
H14I1.40630.68150.90580.069*0.48
C15B0.9445 (12)0.7763 (5)0.9386 (3)0.0462 (13)0.48
H15G1.00120.79420.96810.069*0.48
H15H0.78770.76140.94140.069*0.48
H15I0.96110.82300.91700.069*0.48
C12A0.9693 (6)0.7850 (2)0.75919 (11)0.0520 (9)
H12D1.12930.78850.75430.078*
H12E0.91520.83950.77090.078*
H12F0.89530.77220.73060.078*
C13A1.1925 (9)0.4474 (2)0.88913 (15)0.0889 (16)
H13C1.18610.40280.91070.107*
H13D1.30260.44670.86630.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0276 (4)0.0498 (5)0.0649 (5)0.0004 (4)0.0030 (4)0.0004 (4)
C10.0256 (16)0.0303 (16)0.0412 (17)0.0049 (14)0.0028 (14)0.0051 (14)
C20.0289 (16)0.0327 (16)0.0403 (17)0.0018 (14)0.0020 (14)0.0068 (14)
C30.0228 (14)0.0345 (16)0.0449 (17)0.0037 (15)0.0040 (13)0.0004 (15)
C40.0344 (18)0.0306 (16)0.0532 (19)0.0034 (15)0.0054 (16)0.0015 (15)
C50.0431 (19)0.0285 (16)0.0432 (18)0.0067 (15)0.0044 (16)0.0083 (14)
C60.0263 (15)0.0369 (17)0.0372 (16)0.0071 (15)0.0050 (14)0.0029 (14)
C70.051 (2)0.0402 (19)0.046 (2)0.0000 (17)0.0070 (18)0.0090 (16)
C80.094 (3)0.051 (2)0.041 (2)0.010 (2)0.013 (2)0.0008 (17)
C90.127 (4)0.053 (2)0.059 (3)0.018 (3)0.013 (3)0.005 (2)
C100.077 (3)0.0359 (19)0.068 (2)0.003 (2)0.007 (2)0.0039 (18)
C110.0292 (16)0.0320 (16)0.0495 (18)0.0028 (15)0.0000 (15)0.0026 (15)
C120.051 (2)0.047 (2)0.0461 (19)0.0050 (18)0.0036 (18)0.0039 (16)
C130.089 (3)0.060 (2)0.061 (2)0.010 (3)0.026 (2)0.002 (2)
C140.056 (2)0.0362 (18)0.065 (2)0.0034 (17)0.003 (2)0.0113 (17)
C150.0369 (19)0.044 (2)0.096 (3)0.0079 (18)0.005 (2)0.011 (2)
Cl1A0.0273 (4)0.0734 (6)0.0428 (4)0.0024 (4)0.0038 (4)0.0059 (4)
C2A0.0239 (15)0.0372 (16)0.0340 (16)0.0006 (13)0.0011 (13)0.0088 (13)
C3A0.0222 (14)0.054 (2)0.0334 (16)0.0012 (16)0.0013 (13)0.0075 (16)
C4A0.0354 (18)0.062 (2)0.0371 (17)0.0020 (18)0.0024 (16)0.0217 (17)
C5A0.044 (2)0.0458 (19)0.049 (2)0.0010 (17)0.0041 (16)0.0180 (17)
C6A0.0301 (17)0.0368 (18)0.0442 (18)0.0043 (15)0.0017 (15)0.0124 (15)
C7A0.062 (2)0.0309 (18)0.062 (2)0.0065 (19)0.026 (2)0.0100 (17)
C8A0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C9A0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C10A0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C11A0.0317 (16)0.0375 (17)0.0283 (15)0.0021 (15)0.0019 (13)0.0042 (13)
C14A0.037 (2)0.050 (3)0.051 (2)0.011 (3)0.0151 (18)0.023 (2)
C15A0.037 (2)0.050 (3)0.051 (2)0.011 (3)0.0151 (18)0.023 (2)
C1A0.0210 (14)0.0341 (16)0.0310 (15)0.0010 (13)0.0014 (13)0.0045 (13)
C8B0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C9B0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C10B0.051 (3)0.056 (2)0.0415 (17)0.005 (2)0.0182 (18)0.0160 (15)
C14B0.037 (2)0.050 (3)0.051 (2)0.011 (3)0.0151 (18)0.023 (2)
C15B0.037 (2)0.050 (3)0.051 (2)0.011 (3)0.0151 (18)0.023 (2)
C12A0.044 (2)0.071 (2)0.0409 (19)0.000 (2)0.0039 (16)0.0043 (18)
C13A0.129 (4)0.050 (2)0.087 (3)0.035 (3)0.033 (3)0.014 (2)
Geometric parameters (Å, º) top
Cl2—C31.838 (3)C4A—H4A20.9900
C1—C21.538 (4)C5A—C6A1.531 (4)
C1—C61.538 (4)C5A—H5A10.9900
C1—C111.565 (4)C5A—H5A20.9900
C1—H11.0000C6A—C7A1.521 (4)
C2—C31.499 (4)C6A—C1A1.549 (4)
C2—H210.9900C6A—H6A1.0000
C2—H220.9900C7A—C13A1.326 (5)
C3—C121.508 (4)C7A—C8A1.451 (9)
C3—C41.515 (4)C7A—C8B1.518 (10)
C4—C51.519 (4)C8A—C9A1.515 (8)
C4—H410.9900C8A—H8A10.9900
C4—H420.9900C8A—H8A20.9900
C5—C61.528 (4)C9A—C10A1.507 (9)
C5—H510.9900C9A—H9A10.9900
C5—H520.9900C9A—H9A20.9900
C6—C71.504 (4)C10A—C11A1.549 (7)
C6—H61.0000C10A—H10C0.9900
C7—C131.331 (5)C10A—H10D0.9900
C7—C81.488 (5)C11A—C14A1.481 (7)
C8—C91.507 (5)C11A—C15B1.506 (8)
C8—H810.9900C11A—C15A1.528 (7)
C8—H820.9900C11A—C10B1.547 (6)
C9—C101.465 (5)C11A—C1A1.550 (4)
C9—H910.9900C11A—C14B1.557 (8)
C9—H920.9900C14A—H14D0.9800
C10—C111.548 (4)C14A—H14E0.9800
C10—H10A0.9900C14A—H14F0.9800
C10—H10B0.9900C15A—H15D0.9800
C11—C151.510 (4)C15A—H15E0.9800
C11—C141.536 (4)C15A—H15F0.9800
C12—H12A0.9800C1A—H1A1.0000
C12—H12B0.9800C8B—C9B1.583 (9)
C12—H12C0.9800C8B—H8B10.9900
C13—H13A0.9500C8B—H8B20.9900
C13—H13B0.9500C9B—C10B1.500 (10)
C14—H14A0.9800C9B—H9B10.9900
C14—H14B0.9800C9B—H9B20.9900
C14—H14C0.9800C10B—H10E0.9900
C15—H15A0.9800C10B—H10F0.9900
C15—H15B0.9800C14B—H14G0.9800
C15—H15C0.9800C14B—H14H0.9800
Cl1A—C3A1.837 (3)C14B—H14I0.9800
C2A—C3A1.527 (4)C15B—H15G0.9800
C2A—C1A1.528 (4)C15B—H15H0.9800
C2A—H2A10.9900C15B—H15I0.9800
C2A—H2A20.9900C12A—H12D0.9800
C3A—C4A1.518 (4)C12A—H12E0.9800
C3A—C12A1.527 (4)C12A—H12F0.9800
C4A—C5A1.501 (4)C13A—H13C0.9500
C4A—H4A10.9900C13A—H13D0.9500
C2—C1—C6107.8 (2)C4A—C5A—H5A2109.2
C2—C1—C11112.5 (2)C6A—C5A—H5A2109.2
C6—C1—C11115.4 (2)H5A1—C5A—H5A2107.9
C2—C1—H1106.9C7A—C6A—C5A108.3 (2)
C6—C1—H1106.9C7A—C6A—C1A114.4 (2)
C11—C1—H1106.9C5A—C6A—C1A111.1 (2)
C3—C2—C1116.4 (2)C7A—C6A—H6A107.6
C3—C2—H21108.2C5A—C6A—H6A107.6
C1—C2—H21108.2C1A—C6A—H6A107.6
C3—C2—H22108.2C13A—C7A—C8A117.7 (5)
C1—C2—H22108.2C13A—C7A—C8B127.9 (6)
H21—C2—H22107.3C8A—C7A—C8B14.9 (5)
C2—C3—C12111.5 (3)C13A—C7A—C6A118.8 (4)
C2—C3—C4112.0 (2)C8A—C7A—C6A123.3 (5)
C12—C3—C4112.5 (3)C8B—C7A—C6A113.0 (5)
C2—C3—Cl2107.7 (2)C7A—C8A—C9A114.8 (6)
C12—C3—Cl2106.2 (2)C7A—C8A—H8A1108.6
C4—C3—Cl2106.4 (2)C9A—C8A—H8A1108.6
C3—C4—C5113.1 (2)C7A—C8A—H8A2108.6
C3—C4—H41109.0C9A—C8A—H8A2108.6
C5—C4—H41109.0H8A1—C8A—H8A2107.6
C3—C4—H42109.0C10A—C9A—C8A116.1 (6)
C5—C4—H42109.0C10A—C9A—H9A1108.3
H41—C4—H42107.8C8A—C9A—H9A1108.3
C4—C5—C6110.9 (2)C10A—C9A—H9A2108.3
C4—C5—H51109.5C8A—C9A—H9A2108.3
C6—C5—H51109.5H9A1—C9A—H9A2107.4
C4—C5—H52109.5C9A—C10A—C11A120.6 (6)
C6—C5—H52109.5C9A—C10A—H10C107.2
H51—C5—H52108.0C11A—C10A—H10C107.2
C7—C6—C5110.2 (2)C9A—C10A—H10D107.2
C7—C6—C1117.5 (2)C11A—C10A—H10D107.2
C5—C6—C1109.3 (2)H10C—C10A—H10D106.8
C7—C6—H6106.4C14A—C11A—C15B128.8 (5)
C5—C6—H6106.4C14A—C11A—C15A109.8 (4)
C1—C6—H6106.4C15B—C11A—C15A24.2 (4)
C13—C7—C8120.6 (3)C14A—C11A—C10B80.1 (5)
C13—C7—C6119.3 (3)C15B—C11A—C10B107.7 (5)
C8—C7—C6120.1 (3)C15A—C11A—C10B123.4 (5)
C7—C8—C9111.2 (3)C14A—C11A—C10A114.2 (5)
C7—C8—H81109.4C15B—C11A—C10A79.8 (4)
C9—C8—H81109.4C15A—C11A—C10A101.9 (4)
C7—C8—H82109.4C10B—C11A—C10A35.1 (3)
C9—C8—H82109.4C14A—C11A—C1A111.2 (3)
H81—C8—H82108.0C15B—C11A—C1A109.9 (4)
C10—C9—C8115.7 (4)C15A—C11A—C1A111.6 (4)
C10—C9—H91108.4C10B—C11A—C1A115.7 (3)
C8—C9—H91108.4C10A—C11A—C1A107.8 (3)
C10—C9—H92108.4C14A—C11A—C14B27.0 (3)
C8—C9—H92108.4C15B—C11A—C14B107.2 (5)
H91—C9—H92107.4C15A—C11A—C14B85.0 (4)
C9—C10—C11120.4 (3)C10B—C11A—C14B102.9 (4)
C9—C10—H10A107.2C10A—C11A—C14B132.5 (5)
C11—C10—H10A107.2C1A—C11A—C14B113.0 (4)
C9—C10—H10B107.2C11A—C14A—H14D109.5
C11—C10—H10B107.2C11A—C14A—H14E109.5
H10A—C10—H10B106.9C11A—C14A—H14F109.5
C15—C11—C14108.2 (3)C11A—C15A—H15D109.5
C15—C11—C10112.1 (3)C11A—C15A—H15E109.5
C14—C11—C10103.3 (3)C11A—C15A—H15F109.5
C15—C11—C1111.9 (3)C2A—C1A—C6A108.2 (2)
C14—C11—C1110.6 (2)C2A—C1A—C11A112.4 (2)
C10—C11—C1110.3 (2)C6A—C1A—C11A115.7 (2)
C3—C12—H12A109.5C2A—C1A—H1A106.7
C3—C12—H12B109.5C6A—C1A—H1A106.7
H12A—C12—H12B109.5C11A—C1A—H1A106.7
C3—C12—H12C109.5C7A—C8B—C9B110.4 (6)
H12A—C12—H12C109.5C7A—C8B—H8B1109.6
H12B—C12—H12C109.5C9B—C8B—H8B1109.6
C7—C13—H13A120.0C7A—C8B—H8B2109.6
C7—C13—H13B120.0C9B—C8B—H8B2109.6
H13A—C13—H13B120.0H8B1—C8B—H8B2108.1
C11—C14—H14A109.5C10B—C9B—C8B117.5 (7)
C11—C14—H14B109.5C10B—C9B—H9B1107.9
H14A—C14—H14B109.5C8B—C9B—H9B1107.9
C11—C14—H14C109.5C10B—C9B—H9B2107.9
H14A—C14—H14C109.5C8B—C9B—H9B2107.9
H14B—C14—H14C109.5H9B1—C9B—H9B2107.2
C11—C15—H15A109.5C9B—C10B—C11A112.8 (5)
C11—C15—H15B109.5C9B—C10B—H10E109.0
H15A—C15—H15B109.5C11A—C10B—H10E109.0
C11—C15—H15C109.5C9B—C10B—H10F109.0
H15A—C15—H15C109.5C11A—C10B—H10F109.0
H15B—C15—H15C109.5H10E—C10B—H10F107.8
C3A—C2A—C1A115.7 (2)C11A—C14B—H14G109.5
C3A—C2A—H2A1108.4C11A—C14B—H14H109.5
C1A—C2A—H2A1108.4H14G—C14B—H14H109.5
C3A—C2A—H2A2108.4C11A—C14B—H14I109.5
C1A—C2A—H2A2108.4H14G—C14B—H14I109.5
H2A1—C2A—H2A2107.4H14H—C14B—H14I109.5
C4A—C3A—C2A111.2 (2)C11A—C15B—H15G109.5
C4A—C3A—C12A113.5 (2)C11A—C15B—H15H109.5
C2A—C3A—C12A110.6 (2)H15G—C15B—H15H109.5
C4A—C3A—Cl1A107.5 (2)C11A—C15B—H15I109.5
C2A—C3A—Cl1A107.83 (19)H15G—C15B—H15I109.5
C12A—C3A—Cl1A105.9 (2)H15H—C15B—H15I109.5
C5A—C4A—C3A112.8 (2)C3A—C12A—H12D109.5
C5A—C4A—H4A1109.0C3A—C12A—H12E109.5
C3A—C4A—H4A1109.0H12D—C12A—H12E109.5
C5A—C4A—H4A2109.0C3A—C12A—H12F109.5
C3A—C4A—H4A2109.0H12D—C12A—H12F109.5
H4A1—C4A—H4A2107.8H12E—C12A—H12F109.5
C4A—C5A—C6A112.2 (3)C7A—C13A—H13C120.0
C4A—C5A—H5A1109.2C7A—C13A—H13D120.0
C6A—C5A—H5A1109.2H13C—C13A—H13D120.0

Experimental details

Crystal data
Chemical formulaC15H25Cl
Mr240.80
Crystal system, space groupOrthorhombic, P212121
Temperature (K)180
a, b, c (Å)6.0470 (2), 15.7158 (7), 29.6845 (12)
V3)2821.02 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.65 × 0.24 × 0.21
Data collection
DiffractometerOxford Diffraction CCD Xcalibur
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2006)
Tmin, Tmax0.756, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
23369, 6222, 3666
Rint0.047
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.132, 1.01
No. of reflections6222
No. of parameters294
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.39
Absolute structureFlack (1983), based on 2652 Friedel pairs
Absolute structure parameter0.11 (7)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

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